Reaktion #1483077

ord-7d57691e8f6b4d8ca9c8631a0e278a01

Reaktionsgleichung

COC(=O)c1ccc2c(c1)c(Cc1ccc(NC(=O)c3ccccc3)cc1)cn2C
3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester
[Na+].[OH-]
sodium hydroxide
CO
methanol
O
water
Cn1cc(Cc2ccc(NC(=O)c3ccccc3)cc2)c2cc(C(=O)O)ccc21
3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid
Ausbeute 98.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenconcentrated in vacuo
  2. 2
    workup.ADDITIONThe remaining residue was diluted with ethyl acetate (20 mL)
  3. 3
    Waschenwashed with 1N HCl (20 mL)
  4. 4
    TrocknenThe organic layer was dried over MgSO4
  5. 5
    Filtrationfiltered
  6. 6
    Einengenconcentrated

Vorschrift

A solution of 3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester (69 mg, 0.17 mmol), sodium hydroxide (21 mg, 0.52 mmol), methanol (3 mL), water (1 mL) and THF (3 mL) was heated to 60° C. for 24 hr. The reaction solution was then cooled to room temperature and concentrated in vacuo. The remaining residue was diluted with ethyl acetate (20 mL) and washed with 1N HCl (20 mL). The organic layer was dried over MgSO4, filtered and concentrated to provide 3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid (64 mg, 98% yield).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08900565B2uspto-grants-2014_12